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Volume 69 
Part 3 
Pages o428-o429  
March 2013  

Received 18 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.066
wR = 0.190
Data-to-parameter ratio = 17.9
Details
Open access

(2E)-1-(2,4-Dimethylquinolin-3-yl)-3-phenylprop-2-en-1-one

aDepartment of Chemistry, BITS, Pilani-K. K. Birla Goa Campus, Goa 403 726, India,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

Two independent molecules comprise the asymmetric unit of the title compound, C20H17NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two molecules]. The conformation about each of the ethylene bonds [1.329 (3) and 1.318 (3) Å] is E. The crystal structure features a combination of C-H...N, C-H...[pi] and [pi]-[pi] contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024 (19) Å], generating a three-dimensional network.

Related literature

For background details and the biological application of quinoline and quinoline chalcones, see: Joshi et al. (2011[Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.]); Prasath & Bhavana (2012[Prasath, R. & Bhavana, P. (2012). Heteroat. Chem. 23, 525-530.]); Kalanithi et al. (2012[Kalanithi, M., Rajarajan, M., Tharmaraj, P. & Sheela, C. D. (2012). Spectrochim. Acta A, 87, 155-162.]); Prasath et al. (2013[Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013). J. Organomet. Chem. 726, 62-70.]). For the structures of the isomorphous chloro- and methyl-benzene derivatives, see: see: Prasath et al. (2011[Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o796-o797.], 2012[Prasath, R., Bhavana, P. & Butcher, R. J. (2012). Acta Cryst. E68, o1501.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17NO

  • Mr = 287.35

  • Triclinic, [P \overline 1]

  • a = 11.1295 (9) Å

  • b = 11.5764 (8) Å

  • c = 13.3989 (11) Å

  • [alpha] = 96.176 (6)°

  • [beta] = 112.900 (8)°

  • [gamma] = 96.533 (6)°

  • V = 1558.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.764, Tmax = 1.000

  • 14138 measured reflections

  • 7191 independent reflections

  • 3395 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.190

  • S = 1.05

  • 7191 reflections

  • 401 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C15-C20 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C14-H14...N2 0.93 2.59 3.463 (3) 156
C7-H7C...Cg1i 0.96 2.86 3.662 (3) 142
C39-H39...Cg2ii 0.93 2.88 3.679 (3) 145
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5294 ).


Acknowledgements

PB and RP gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), India, for research grant 02 (0076)/12/EMR-II and Senior Research Fellowship (09/919/(0014)/2012 EMR-I), respectively. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.  [CrossRef] [PubMed] [ChemPort]
Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.  [CrossRef] [ChemPort]
Kalanithi, M., Rajarajan, M., Tharmaraj, P. & Sheela, C. D. (2012). Spectrochim. Acta A, 87, 155-162.  [ChemPort]
Prasath, R. & Bhavana, P. (2012). Heteroat. Chem. 23, 525-530.  [ISI] [CrossRef] [ChemPort]
Prasath, R., Bhavana, P. & Butcher, R. J. (2012). Acta Cryst. E68, o1501.  [CSD] [CrossRef] [details]
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o796-o797.  [CSD] [CrossRef] [ChemPort] [details]
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013). J. Organomet. Chem. 726, 62-70.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o428-o429   [ doi:10.1107/S1600536813004765 ]

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